Andy Warhol’s Web 2.0

If Andy Warhol were alive today, you kind of get the feeling that he would draw portraits of the Web 2.0 elite, don’t you? Well, over the weekend, I broke into St. John the Baptist Byzantine Catholic Cemetery, where Warhol is buried, dug him up, shoved electrical cords into his nostrils, and successfully shocked him back to life. By dangling a donut in front of his now skeletal face, I was able to coerce him into drawing portraits of today’s leading Web 2.0. figures. Warhol’s work, and my commentary, are what follows:

Kevin Rose

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Ah, the power of bully pulpits. The first time Kevin Rose really took advantage of his bully pulpit, he propelled his career in unimaginable ways. Flashback to 2004. Rose introduced digg.com to the world during a brief segment of G4TV’s Screen Savers, immediately ushering in a new era of online news gathering and consumption.

Sometime later, Rose made arguably the best business decision of his life when he elected not to sell digg to Weblogs Inc. By holding onto digg, Rose could more easily draw attention to himself and increase his social capital, making future angel investments and product launches easier.

So, how powerful is Rose’s bully pulpit now? It’s apparently so powerful that he can bring about major acquisitions just by suggesting them on Diggnation. In 2009, Rose advised Intuit to buy Mint.com, and they listened, bagging the site for $140 million that September. Like all of today’s Web 2.0 elite, Kevin’s dreams broke the boundaries of his fears long ago. Will yours?

Veronica Belmont

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Veronica Belmont bounced onto the web scene in 2006 as the producer and co-host of CNET’s BuzzOutLoud and never looked back. At CNET, she slowly chipped away at more responsibility until she was named a full fledged co-host of the show in August of 2006. In 2007, she left CNET to host Mahalo Daily at Mahalo.com, where she was given full creative control of the show’s content.

Today, Veronica hosts Qore (a monthly interactive magazine about the PS3 for Sony) and Tekzilla (a weekly tech help and how-to show on Revision3.com). Belmont is at a stage in her career where her success will only engender further success. As her web celebrity status keeps ballooning, she’ll continue to sit on panels (like the Geek Girls Exist! panel at Comic-Con) and guest host TV shows (like G4’s Attack of the Show). But don’t let Veronica’s on-camera talents fool you into thinking she’s one-dimensional: she can draw an audience in with her penmanship just as easily as she can by speaking. Veronica has written pieces for Slate, DoubleX, MaximumPC, PC Gamer Magazine, and Engadget.

Jason Calacanis

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This SEO king to rule them all was the poster-child of Web 1.0 and today stands proudly as the face of Web 2.0 as well. In a way, that makes him sort of like Patrick Stewart, if we consider Web 1.0 and Web 2.0 as separate franchises. (If you’re not quite getting the analogy, Stewart is the icon of two franchises–Star Trek and X-Men. Ok, geek moment over. Let‘s move on.) Early in his career, Calacanis was offered $20 million for his first company, Silicon Alley Reporter. A consummate gambler, he turned the offer down. Whoops. Silicon Alley Reporter popped with the bubble, and a broken Calacanis turned to drinking, as many of us do in times of despair. After a few months of post-traumatic stress, he dragged himself off the floor and got back in the game, more driven and fiery than ever. He wasn’t just going to build something significant; he was going to build something revolutionary. Something that would forever change the fabric of the Internet. And he did. Weblogs Inc., a startup he co-founded with Brian Alvey in 2004, brought blogging to the forefront of our culture and spawned sites like Engadget, Autoblog, and TVSquad–all originally under the umbrella of Calacanis’ company.

2005 rolled around, and Calacanis was ready to cash in his chips. He sold Weblogs Inc. for about 26 million, became an EIR at Sequoia Capital, and founded Mahalo in 2007. The rest, as the cliché makers say, is history, but if you know anything about Jcal, you can be damn sure he’s just getting started. Think streaming video and captivating conferences.

Felicia Day

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Have you ever been told you weren’t good enough? Told that you would never succeed? Did you have the grit to push forward anyway? To find the dawn in your darkest hour? To build your own box if you couldn’t squeeze into a pre-existing one? If you answered “yes” to any of those questions, then you know the struggle of Felicia Day.

Day’s road to stardom was ripe with landmines. After playing a handful of supporting characters in a few films and TV shows, Day tried her luck at snagging a lead role in a major film but was rejected time and again. Fed up with stuffy casting directors and producers with narrow world views, Day went around the system to create and write “The Guild,” a comedy web series that examines the lives of an online group addicted to a MMORPG video game.

“The Guild” has become so successful that it (ironically) could probably be flipped into an actual TV feature now, much like “How It Should Have Ended” (which inked a deal with Starz in 2009) and other web shows. But would Day even consider that path? Knock on Felicia’s door and ask her. Like her character Codex was when Warlock Zaboo showed up unannounced at her doorstep in the pilot episode of Day’s series, she’ll doubtlessly be happy to see you.

Andrew Keen

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When he isn’t thrashing Wikipedia founder Jimmy Wales in public debates, this self-described anti-Christ of Silicon Valley is giving keynote speeches to help people understand exactly how the “Internet is killing our culture.” His book, The Cult of the Amateur, discusses how social networking, blogs, and wikis are pushing our culture back into the dark ages and effecting the slow destruction of civilization.

Keen often points out Twitter’s tendency to turn people into either sheep or shepherds. Says Keen, “On Twitter, you’re either a follower or you’re followed.” But I think a statement like that is question-begging. What about the people who mass follow and have loads of followers as a result? Are they sheep and shepherds simultaneously? How would Mr. Keen classify these people? (Hint: probably as whores)

Jolie O’Dell

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Tech blogger Jolie O’Dell has a storied journalistic career. She’s worked at newspapers, magazines, marketing agencies, and publishing houses. So, it’s probably safe to assume she’s learned a thing or two about reporting from multiple angles. After a lengthy stint as a writer and community manager at ReadWriteWeb, O’Dell joined Mashable as a social media and tech reporter in 2010.

O’Dell is particularly adept at writing personality profile pieces, but truth be told, if you hand Jolie a pen, she can probably write anything on any topic. She can also play a mean bass guitar and scarf down a cheeseburger like nobody’s business.

Leo Laporte

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You probably already knew that Leo Laporte was a pioneer of podcasting (or netcasting as he likes to call it), but did you also know that he was an obsessive traveler? According to an August L.A. Times piece, Laporte is on the road or in the sky constantly, with stops in cities like Burbank, Vegas, and Austin. He’s been everywhere, man.

Given the success of Laporte’s netcast network, TwiT.Tv, you might also be surprised to learn that he’s turned down major advertisers like Apple and Microsoft. Laporte feels that a divisive major advertiser could taint his programs by showing bias, so he instead relies on fan donations to make up for the lost revenue. Laporte’s end goal is to have 24 hours of unique, original programming on the web. Now, chew on this for a moment: if one fan gave Leo a Hawaiian shirt for each one of those hours, he would have 8,760 after a year (or 8,784 in a leap year). And with 8,760 Hawaiian shirts being pumped into his wardrobe every year, Leo could donate his already existing collection of 1,171,383 Hawaiian shirts to East Timor and dress the entire population.

Gary Vaynerchuk

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When Gary Vaynerchuk isn’t getting prank-called by Sean Percival at five o’clock in the morning, he’s busy running the world’s most popular wine blog, Wine Library TV. Gary’s hyperkinetic, in-your-face style has inspired legions of devout “Vayniacs” to take gambles in their lives so they can maximize their worth.

Vaynerchuk runs the largest online social community for wine lovers, corkd.com, and his retail website, WineLibrary.com, pulls in over $60 million annually. Gary V’s first non-wine book, Crush It! Why Now is the Time to Cash in on your Passion, quickly became a New York Times bestseller and left many hungry for its planned nine sequels. If you’ve somehow managed to use the Internet without ever coming across a single Vaynerchuk video, I encourage you to get “Vaynerized” by firing up Wine Library TV and watching all one-thousand-something episodes in a single sitting. Only then can you be fully brainwashed.

Sean Percival

When Sean Percival isn’t prank-calling Gary Vaynerchuk at five o’clock in the morning, he’s presumably still awake and attending to his baby, Charlotte. Sean is the founder of Lalawag.com, an LA tech blog that he sold to Jesse Draper in 2010. Truth be told though, Sean never really ran Lalawag. His wife, Laurie, did. All Sean did was higher gophers and tell them to “go for this, go for that,” and he barely even oversaw that. On one occasion, he accidentally hired a monkey he thought was a person. Let me set the scene. Sean was half asleep in Lalawag Studios when a monkey walked in with a sign around its neck that read, “Cannot speak: Strep throat. Capable of baking egg soufflé and doing other gopher-like tasks. Skilled blackjack dealer.” Sean glanced up and mumbled, “You’re hired.”

He awoke the next day to find Lalawag Studios covered in feces and overcooked egg soufflé, which no one had ordered. After giving the monkey a goodbye hug, he booted it back out to the streets and immediately began hunting for an actual gopher to clean the mess up.

Ok, enough crazy talk (although I think “crazy talk” might be a euphemism for reality). What does Sean really do? He’s the Vice President of Online Marketing at MySpace, a position he won after previous stints at Mahalo, Docstoc, and Tsavo. Yes, he’s seen two Jasons and a Mike in his day…all on his journey to become one of the most valuable assets in Silicon Valley. Most startups probably wish they had a Percival or three on board.

iJustine

Justine Ezarik has perhaps done more than any other top-level Youtuber to spread her reach beyond the confines of the video site. She’s a spokesperson for the back-up storage site Mozy and has appeared in three national TV commercials for the company. She also played a photojournalist tasked with covering a bank robbery in the Spike TV show “Kill Point” in 2007, and she convincingly portrayed a 16-year old girl in a 2009 episode of “Law and Order: SVU.” Yes, that’s right. At the age of 25, she successfully depicted a 16-year old girl. Not many can say they were able pull that off.

Like other social media leaders, Justine has helped make “advertising cool again.” Few iJustine fans were offended by her decision to participate in a 2009 Carl’s Jr. campaign that required her to eat a Carl’s Jr. hamburger on camera nor were they bothered by her decision to join the Twitter advertising service Ad.ly with Paul Reubens and many others at the end of ‘09. Justine’s tagline is that she “is the Internet.” Considering she can make a video accumulate 540,000 views just by doing a booty dance to an ipad, is anyone really willing to challenge her claim?

Zack Luye

In the same way that Gary Vaynerchuk has established himself as the wine guru of the Internet, Zack Luye has steadily built a reputation as something of a tea sage. Zack is the host of leading tea maker Adagio Tea’s weekly web show, where he reviews tea blends that viewers send in and discusses Adagio’s latest products.

In 2008, Zack developed a concept for a drink culture review show called “Bottles, Blends, and Brews” and pitched it to Revision3. His initial concept was rejected, but he tweaked it, re-polished it, and sent it back for another look. Revision3 was impressed by the show’s improvements and green-lit its entry into its freshman class of beta shows. Finally, Luye had a platform he could use to force himself and others to ingest the vitamin-rich fluids of the Hudson River. Now, “Bottles, Blends, and Brews” is being released in a super-secret web format. So, what direction will Luye’s career go in next? Well, he’s already directed several music videos and filmed a TV pilot. He also racked up over 20,000 votes on his quest to be the star of a talk show on the OWN network before being asked to take on a yet-to-be-released project inside Oprah’s camp. Earlier this year, Zack won a position as the “quarterback” for creative agency Relentless and is currently filming a web series in the desert. Since Zack is as equally talented in front of a camera as he is behind it, he’ll likely continue to have an assortment of projects to choose from in the future.

Shane Dawson

Shane Dawson’s eccentric comedic style has landed him the praise of critics from across the web. He won a Streamy Award for best Vblogger and was named the 25th most famous web celebrity by Forbes Magazine in 2010. Just how wide is Shane Dawson’s reach on Youtube? It’s so wide that many credit him with single-handedly turning several Youtubers into stars just by mentioning them in his videos. There’s no question, for instance, that a video collaboration with Dfizzy in 2009 helped propel this relatively unknown Youtuber toward stardom.

Perhaps Dawson’s most enduring quality is his steadfast opposition to the growing trend of advertising in Youtube videos. He was one of the few top Youtubers who elected not to become an official Carl’s Jr. spokesperson in 2009. In fact, he created a pointed spoof of the campaign. Like iJustine and other top Youtubers, Dawson may well end up spreading his reach far beyond the Google-owned website.

Julia Allison

Who is Julia Allison? A reporter? An entertainer? A jack of all trades? All of the above? This 2008 Wired Magazine cover girl is quite the Valley chameleon. Allison got her early kicks as a dating columnist for her college newspaper before eventually grabbing a gig as a columnist for Time Out New York. But Allison’s popularity didn’t start to grow vertically until she began appearing as a guest commentator on cable networks like MSNBC, Fox News, and CNN.

In 2008, Allison was asked to deliver the commencement address at a New York city public high school. During her speech, she told the students to dump their significant others before they went off to college, sending the audience into a state of dysphoria.

These days, Allison can be found starring in films like Make Me Young: Youth Knows Knows No Pain, a documentary that exposes the pro-plastic surgery sentiment (read: insanity) of L.A. culture in excruciatingly ghastly detail. When Allison sleeps at night, she slips into dreams so demented they would drive Sigmund Freud to suicide if he were still alive and tried to analyze them.

Loren Feldman

Catch him at the right angle, and he’s the spitting image of Dave Attell. Catch him at the wrong angle, and he’ll punch your lights out. Just ask Julia Allison or Jonathon Schwartz. They’ve both faced the wrath of 1938 Media mogul Loren Feldman’s perfectly powdered-up puppets. But no Web 2.0 figure has been toyed with more by Feldman than Shel Israel, the Twitterville author and former Fast Company TV personality who used microphones leftover from the 1976 set of “The Price is Right.” Feldman successfully turned Isreal’s life into a living hell, and now, he can’t even use Twitter for more than five hours without someone bringing up Feldman’s caricature of him–a loud, obnoxious, buffoon-like creature with an off and on high-pitched, effeminate voice.

Let’s go back to the Attell angle for a moment. Have you ever wondered why some decent programs on Comedy Central are canceled while other hapless shows are allowed to continue on their merry way, sometimes for years? Take Dave Attell’s “Insomniac,” which lasted four seasons and consisted of little more than the comedian walking into bars and chatting with drunk people. Now, what do you think would happen if Attell-look-a-like Loren Feldman pitched a show to Comedy Central with a vastly more creative premise than “Insomniac?” Well, odds are that Comedy Central would turn his show down because creative thinking that travels too far out of bounds is often frowned upon by TV execs. And frankly, that’s more sickening than watching Feldman hose down his Shel puppet every morning.

LisaNova

In 2009, YouTube celebrity Lisa Donovan (LisaNova) had a brilliant thought. She realized that if she created a Youtube channel that combined the talents of leading Youtube stars that it would not only be insanely popular, but also rapidly popular. So, she recruited top Youtubers like Philip DeFranco, Kasseem G, and Andrea Brooks, and with the help of business partner Danny Diamond, launched The Station in July of 2009. The channel was, unsurprisingly, an immediate smash, shooting to 340,000 subscribers in its first two weeks. Some resented the channel on principle; others quickly became obsessed with it. But few doubted the genius of its conception.

Nova’s individual videos have also grown quite popular and led her toward further opportunities. She had a brief stint as a player on MadTV and has been offered several endorsement deals. As the co-founder of the viral video production company Zappin Productions, Donovan has shown to be just as skilled a strategist as she is a performer.

Tay Zonday

If Chocolate Rain composer Adam Bahner (a.k.a. Tay Zonday) was cast as a super-villain in an animated film, he would walk around saying, “Chocolate pain. No one can escape my evil reign.”

Enough said.

Night turned to dawn, and it was time to put Warhol back in his grave. Not an easy sell–not by any stretch.

“Based on what you’ve told me about the future,” said Andy, “there are many more to draw. What of Scoble and Siegler and Pincus and Parr? And the one they call Denton; I must draw his cigar! ”

Love the post.. It is clever and makes some interesting points. I love Andy Warhol, so that brought me to read this article. You are quite a clever person to do this.. Bravo and two thumbs up. Thanks for keeping it real and in perspective.

Enterprise Cometh was founded on a lazy Sunday in 2010 by Will Paoletto and Gideon Von Hideon. (Von Hideon has since resigned from the project due to a bad case of Bogart’s disease. Bogart‘s disease, for those not in the know, is what results when a person has such a deep-rooted obsession with Humphrey Bogart […]